CHEBI:69246 - (−)-larreatricin

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ChEBI Name (−)-larreatricin
ChEBI ID CHEBI:69246
ChEBI ASCII Name (-)-larreatricin
Definition A lignan that consists of a 3,4-dimethyloxolane ring substituted by 4-hydroxyphenyl groups at positions 2 and 5 respectively (the 2S,3R,4S,5S-stereoisomer). Isolated from the roots of Krameria lappacea, it exhibits anti-inflammatory activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C18H20O3
Net Charge 0
Average Mass 284.34960
Monoisotopic Mass 284.14124
InChI InChI=1S/C18H20O3/c1-11-12(2)18(14-5-9-16(20)10-6-14)21-17(11)13-3-7-15(19)8-4-13/h3-12,17-20H,1-2H3/t11-,12+,17-,18-/m0/s1
InChIKey PIBJADPEZQHMQS-CMKMFDCUSA-N
SMILES C[C@H]1[C@@H](C)[C@H](O[C@@H]1c1ccc(O)cc1)c1ccc(O)cc1
Metabolite of Species Details
Krameria lappacea (NCBI:txid228636) Found in root (BTO:0001188). Methylene dichloride extract of dried and ground roots See: PubMed
Roles Classification
Biological Role(s): cyclooxygenase 1 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
NF-kappaB inhibitor
An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-larreatricin (CHEBI:69246) has role anti-inflammatory agent (CHEBI:67079)
(−)-larreatricin (CHEBI:69246) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
(−)-larreatricin (CHEBI:69246) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
(−)-larreatricin (CHEBI:69246) has role NF-κB inhibitor (CHEBI:73240)
(−)-larreatricin (CHEBI:69246) has role plant metabolite (CHEBI:76924)
(−)-larreatricin (CHEBI:69246) is a lignan (CHEBI:25036)
(−)-larreatricin (CHEBI:69246) is a oxolanes (CHEBI:26912)
(−)-larreatricin (CHEBI:69246) is a phenols (CHEBI:33853)
IUPAC Name
4,4'-[(2S,3R,4S,5S)-3,4-dimethyloxolane-2,5-diyl]diphenol
Registry Number Type Source
4236154 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21800856 PubMed citation Europe PMC
Last Modified
13 April 2015